Herbicide mixtures of 3-lower alkyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide and a substituted benzoic acid derivative

ABSTRACT

WHERE X denotes halogen, methoxy or amino and n denotes one of the integers 1, 2, 3 and 4, it being possible for methoxy and halogen or amino and halogen or methoxy, amino and halogen to be present simultaneously. Herbicide compositions of mixtures in the weight ratio of 5:1 to 1:5 of (a) 3-lower alkyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide and (b) a compound of the formula

United States Patent [191 Fischer [4 1 Sept. 2, 1975 HERBICIDE MIXTURES OF 3-LOWER ALKYL-Z,1,3-BENZOTHIADIAZINONE-(4)- 2,2-DIOXIDE AND A SUBSTITUTED BENZOIC ACID DERIVATIVE [75] Inventor: Adolf Fischer, Mutterstadt, Germany [73] Assignee: BASF Aktiengesellschaft,

Ludwigshafen (Rhine), Germany [22] Filed: Jan. 11, 1974 [2]] Appl. N0.: 432,674

Related US. Application Data [62] Division of Ser. No. 343,629, March 22, 1973.

[30] Foreign Application Priority Data Apr. 13, 1972 Germany 2217722 71/114; 71/115; 71/121; 71/124 [51] Int. Cl. A01N 9/12; AOlN 9/24 [58] Field of Search 71/91, 115

[56] References Cited UNITED STATES PATENTS 3/1965 McLane et al 71/115 7/1968 Goebel l/l973 Zeidler et al. 71/91 OTHER PUBLICATIONS Fischer I, I-lerbicidal Compositions Containing etc, (1971), CA 75, No. 75217h,(1971). Fischer II, Herbicidal Compositions, (1971), CA 74, N0. 110,714W, (1971).

Primary Examiner-Glennon H. Hollrah Attorney, Agent, or F irm.lohnston, Keil, Thompson & Shurtleff [5 7] ABSTRACT Herbicide compositions of mixtures in the weight ratio of 5:1 to 1:5 of (a) 3-lower alkyl-2,l,3- benzothiadiazinone-(4)-2,2-dioxide and (b) a compound of the formula 5 Claims, No Drawings HERBICIDE MIXTURES OF S-LOWER ALKYL-2,l,3-BENZOTI-IIADIAZINONE-(4)-2,2- DIOXIDE AND A SUBSTITUTED BENZOIC ACID DERIVATIVE RELATED APPLICATION where R denotes lower alkyl of a maximum of 4 carbon atoms, or its salts, such as alkali metal, alkaline earth metal, ammonium, hydroxyalkylammonium, alkylammonium and hydrazine salts, e.g. salts with sodium, lithium, potassium, calcium, iron, methylammonium, trimethylammonium, ethylammonium, diethanolammonium, ethanolammonium, dimethylamine, dimethylethanolamine, hydrazine and phenylhydrazine, and

b. a compound of the formula where X denotes halogen, methoxy or amino and n denotes one of the integers l, 2, 3 and 4, it being possible for methoxy and halogen or amino and halogen or methoxy, amino and halogen to be present simultaneously, have a herbicidal action superior to that of their individual components.

Active ingredients 0 to k may be applied in amounts of 0.5 to 5 kg per hectare.

The weight ratio of a b, is from 5:1 to 1:5, preferably from 3:1 to 1:3.

The compositions of the invention are suitable'for controlling unwanted plants, e.g. dicotyledonous seed weeds, monocotyledonous grassy seed weeds and Cyperaceae in crops such as cereals, rice, soybeans, Indian corn, potatoes, peas, and beans.

The compositions may be used preand/or postemergence. v

The agents according to the invention may be used mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils and oils of vegetable or mineral origin, and cyclic hydrocarbons such as tetrahydronaphthalene and alkylated naphthalenes are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes or wettable powders by adding water. To prepare emulsions the ingredients as such or dissolved in a solvent may be homogenized in water or organic solvents by means of wetting or dispersing agents, e.g., polyethylene oxide adducts. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent. Oils of various types may be added to ready-to use spray liquors.

Dusts may be prepared by mixing or grinding the active ingredients with a solid carrier, e.g., clay or fertilizers.

Granules may be prepared by bonding the active ingredients to solid carriers.

Directly sprayable dispersions may also be prepared with oils.

The new compounds may be mixed with fertilizers, insecticides, fungacides and other herbicides.

EXAMPLE 1 The plants rice (Oryza sativa), soybeans (Soja hispida), Indian corn (Zea mays), wheat (Triticum aesas solutions, emulsions, suspensions oil dispersions,

tivum), barnyard grass (Echinuchloa crus-galli), giant foxtail (Selaria fizberii), yellow nutsedge (Cyperus esc'ulenlus), common cocklebur (Xantlzium pensylvanicum), wild mustard (Sinapis arvensis), waterplantain (Alisma planlago-aquatic'a), catchweed bedstraw (Galium apurine), chamomile (Matricaria chamvmilla), slender foxtail (Alopecurus myosuroides) and annual bluegrass (Poa annua) were treated at a growth height of 4 to 20 cm with the following individual active ingredients and compositions thereof, each active ingredient and each composition being emulsified or dispersed in 500 liters of water per hectare:

I 2,4'-dinitro-4-trifluoromethyldiphenyl ether, 1.5

and 3 kg per hectare;

II 4'-nitro-2,4,6-trichlorodiphenyl ether, 2 and 3 kg per hectare;

III N-( 1, 1-dimethylpropynyl)-3,5-

dichlorobenzamide, 1 and 3 kg per hectare;

IV 2-( 2-methyl-4-chlorophenoxy)-N- methoxyacetamide, l and 2 kg per hectare;

V 2,3,6-trichlorobenzoic acid, 0.5 and 2 kg per hectare;

VI2-methoxy-3,6-dichlorobenzoic acid, 1.5 and 2 kg per hectare;

VII" 3-isopropyl-2, l ,3-benzthiadiazinone-( 4 )-2,2-

dioxide, 0.5, l, 1.5, 2 and 3 kg per hectare;

1+ VII: 1.5 1.5 kg per hectare;

II VII: 2+ 1 kg per hectare;

III VII: l 2 kg per hectare;

IV VII; 1 1 kg per hectare;

V VII: O.5 1.5 kg per hectare;

VI VII: 1.5 0.5 kg per hectare.

After 8 to 14 days it was ascertained that the compo sitions had a better overallaction than the individual active ingredients, combined with good crop plant compatibility. The results are given below:

Active ingredient I II III IV V VI VII kg/ha l l 2 3 l 1 l 2 0.5 1.5 2 0.5 l l 5 2 l ()ryzu .s'ulim I0 25 I0 0 0 0 0 0 Suja llixpillu I0 5 0 0 0 5 I0 Zea muyx 0 20 0 0 0 0 0 Tl'iliz'um (l.\'li\ll"l 0 20 I0 I5 0 0 0 0 0 Iz'tlrinm'lxluu 65 95 60 90 40 X0 40 l 0 5 5 l0 I0 (ms-gull! Seturiu fabcrii 65 90 60 90 35 70 75 0 5 5 I0 I5 \'p'ru.\' (.t'tlI/LHIHA 45 80 30 55 0 55 5 l0 20 36 45 65 90 XunI/rium 30 65 30 45 25 61) I 55 3U 40 6O 7O 95 Sinupix urrenxix 60 95 40 ()0 60 95 45 90 45 .60 75 95 I00 Alixnmplunlago- 30 I5 30 20 20 45 20 40 75 80 uqm/Iim Galium npurine 25 85 60 85 30 40 60 70 80 Murricuriu 30 95 90 35 50 60 90 95 ('lmnmmi/Iu Alupm'urm 50 95 45 80 5 5 I5 I0 15 nrvua'uruilh'a' luu mmml 55 I00 60 95 5 5 5 5 I0 (I no damage 100 complete destruction Active ingredient I VII II VII III VII 7 IV VII V VII VI VII kg/hu 2.5 1.5 2 I I 2 I I 0.5 1.5 L5 +0.5

()rygu .mliru l0 l0 .S'uju lu'xpizlu l0 5 Zcu nmys 0 Trim-um ucxlirmn 0 l0 lithium-111011 vrux- 90 90 X0 gulli Sclariu filln'rii 90 85 75 ('ypvrux asculonlus I00 95 I00 I00 Xunrhium pt'nx \'li'uniumI I00 I00 I00 I00 Sinuplls' lll' 't'IlA'IA' I00 I00 I00 I00 Alisnul plan/gm I00 90 I00 I00 aqmuiz'u Galimn purine I00 95 Mulricariu I 00 95 chunmmillu Alopm'urux mymuroidm 75 I'm! unnml 80 80 0 no damage I00 complete destruction EXAMPLE 2 50 position I II had better crop plant compatibility and a better herbicidal action than its individual compo- In the open the crop plant soybeans (So a lusprda) ems and n and Indian corn (Zea mays) and the unwanted plants The results are given below: barnyard grass (Echmochloa crus-galli), giant foxtall (Selaria faberii), yellow nutsedge (Cyperus esculentus), wild mustard (Sin apis arvensis), common cocklebur 55 Active ingredient l n l+ ll (Xanrlu'um pensylvanicum), catchweed bedstraw kg/h 2 2 (NH-3 (Galium aparine), chamomile (M arricaria chamomilla), tsvju hispida 0 0 0 l0 0 perennial ryegrass (Lolium perenne) and bluegrass W 0 0 0 l5 0 (Poa trivialis) are treated postemergence with the folgr- 10 80 lowing individual active ingredients and composition 60 Semriufillu'rri 15 2o 45 80 (.yperns csculenlus 40 75 l0 10 90 thereof Sinapix m'vmsix 40 so 20 30 100 I 3-1 0p py n l zm n )-2,2- Xanrhium pensylvunicum 5o 90 s 10 100 i 7 Guliumu xn'ine 45 80 l0 I0 85 f 0 2 kg per h k Mulriuuiu clummmillu 50 80 5 IO ll 3-ammo-2,5-dichlorobenzoic acid, 1.3 and 2 g per Mum" 0 0 40 70 70 65 mi lriridlis 0 0 so 80 90 hectare; I II 0.7 1.3 kg per hectare. After 10 to 14 days it was ascertained that the c0m- 0 no damage complete destruction Active ingredient I ll lll [V l lV H lV lll IV kg/hzl 0.4 0.3 0.5 0.5 0.4 0.5 0.3 +0.5 0.5 0.5

Trilic'um aux/[rum 5 l 0 0 0 0 Harden"! \ulgurv 0 5 0 0 0 0 0 St'c'alc u'rcule 0 5 0 0 0 0 0 lawn grass 0 0 0 0 0 0 0 Sinupis urvz'nsis 30 35 I5 25 80 90 70 (iulevpxit lcrm/u'! 25 30 75 85 75 Gulium uparilu' Z0 I5 90 I00 85 Kudziu scupuria 25 25 I5 20 70 80 8O Lunu'um [Jlll'plll'L'l/Hl 30 25 l() 80 90 90 Lillmypcrmum uflit'inulc 25 30 20 25 75 .90 85 Mutriulriu clmmumillu 20 30 20 35 80 100 75 Amumnl/mx relruflatua' 30 35 25 30 90 I00 95 XunI/zium pensylrunit'um 20 25 20 40 85 95 90 no damage I00 complete destruction where R denotes lower alkyl of a maximum of 4 carbon atoms, or an alkali metal, lower alkylammonium, lower hydroxyalkyl-ammonium, or lower alkyl lower hydroxyalkyl ammonium salt thereof, and

b. 2,3,6-trichlorobenzoic acid, 2-methoxy-3,6-dichlorobenzoic acid, 3-amin0-2,5-dichlorobenzoic acid, or 2-methoxy-3,5,6-trichlorobenzoic acid in a weight ratio ofa to b in the range of 3:1 to 1:3.

2. A herbicide composition as claimed in claim 1 wherein compound (b) is 3-amino-2,S-dichlorobenzoic acid.

3. A herbicide composition as claimed in claim 2 wherein compound (a) is 3-isopropyl-2,l,3- benzothiadiazinone-(4)-2,2-dioxide.

4. A herbicide composition as claimed in claim 1 wherein compound (b) is 2,3,6-trichlorobenzoic acid.

5. A herbicide composition as claimed in claim 1 wherein compound (b) is 2-methoxy-3 ,6- dichlorobenzoic acid or 2-methoxy-3,5,6- 

1. A HERBICIDE COMPOSITION COMPRISING AN INERT SOLID OR LIQUID CARRIER HAVING DISPERSED THEREIN A HERBICIDALLY EFFECTIVE AMOUNT OF HERBIDICIDES CONSISTING ESSENTIALLY OF A. A COMPOUND OF THE FORMULA
 2. A herbicide composition as claimed in claim 1 wherein compound (b) is 3-amino-2,5-dichlorobenzoic acid.
 3. A herbicide composition as claimed in claim 2 wherein compound (a) is 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide.
 4. A herbicide composition as claimed in claim 1 wherein compound (b) is 2,3,6-trichlorobenzoic acid.
 5. A herbicide composition as claimed in claim 1 wherein compound (b) is 2-methoxy-3,6-dichlorobenzoic acid or 2-methoxy-3,5,6-trichlorobenzoic acid. 